PL2477967T3 - Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process - Google Patents
Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that processInfo
- Publication number
- PL2477967T3 PL2477967T3 PL10760917T PL10760917T PL2477967T3 PL 2477967 T3 PL2477967 T3 PL 2477967T3 PL 10760917 T PL10760917 T PL 10760917T PL 10760917 T PL10760917 T PL 10760917T PL 2477967 T3 PL2477967 T3 PL 2477967T3
- Authority
- PL
- Poland
- Prior art keywords
- benzodiazepine
- imidazo
- pyridinyl
- bromo
- preparing
- Prior art date
Links
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- CYHWMBVXXDIZNZ-KRWDZBQOSA-N methyl 3-[(4s)-8-bromo-1-methyl-6-pyridin-2-yl-4h-imidazo[1,2-a][1,4]benzodiazepin-4-yl]propanoate Chemical compound N([C@H](C1=NC=C(C)N1C1=CC=C(Br)C=C11)CCC(=O)OC)=C1C1=CC=CC=N1 CYHWMBVXXDIZNZ-KRWDZBQOSA-N 0.000 title 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09011914A EP2305647A1 (en) | 2009-09-18 | 2009-09-18 | Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process |
| EP10760917.4A EP2477967B1 (en) | 2009-09-18 | 2010-09-15 | Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process |
| PCT/EP2010/005668 WO2011032692A1 (en) | 2009-09-18 | 2010-09-15 | Process for preparing 3-[(4s)-8-bromo-1-methyl-6-(2-pyridinyl)-4h-imidazol[1,2-a][1,4]benzodiazepine-4-yl]propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL2477967T3 true PL2477967T3 (en) | 2016-04-29 |
Family
ID=41467237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL10760917T PL2477967T3 (en) | 2009-09-18 | 2010-09-15 | Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US9156842B2 (en) |
| EP (2) | EP2305647A1 (en) |
| JP (1) | JP5801309B2 (en) |
| KR (1) | KR101801735B1 (en) |
| CN (1) | CN102753525B (en) |
| AU (1) | AU2010294873B2 (en) |
| BR (1) | BR112012006053B1 (en) |
| CA (1) | CA2774018C (en) |
| DK (1) | DK2477967T3 (en) |
| ES (1) | ES2555233T3 (en) |
| HK (1) | HK1173437A1 (en) |
| HR (1) | HRP20151316T1 (en) |
| HU (1) | HUE028298T2 (en) |
| MX (2) | MX341093B (en) |
| PL (1) | PL2477967T3 (en) |
| PT (1) | PT2477967E (en) |
| RU (1) | RU2551848C2 (en) |
| WO (1) | WO2011032692A1 (en) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2081921T3 (en) | 2006-07-10 | 2011-03-31 | Paion Uk Ltd | Short-acting benzodiazepine salts and their polymorphic forms |
| EP2305647A1 (en) | 2009-09-18 | 2011-04-06 | PAION UK Limited | Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process |
| EP2450039A1 (en) | 2010-11-08 | 2012-05-09 | PAION UK Ltd. | Dosing regimen for sedation with CNS 7056 (Remimazolam) |
| CN102964349A (en) * | 2011-08-31 | 2013-03-13 | 江苏恒瑞医药股份有限公司 | Tosilate of benzodiazepine derivative, its crystal forms, their preparation method and application |
| SG11201501358SA (en) | 2012-08-31 | 2015-04-29 | Paion Uk Ltd | Method for administering hypnotic/sedative agent |
| AR094963A1 (en) | 2013-03-04 | 2015-09-09 | Ono Pharmaceutical Co | EXCELLENT OXIDATION REACTION IN THE CONVERSION INDEX |
| CN103232454A (en) * | 2013-05-05 | 2013-08-07 | 王元青 | Medicine for treating mental disease |
| CN103230595B (en) * | 2013-05-05 | 2014-10-08 | 李友香 | Composition for treating mental diseases |
| CN105726495B (en) * | 2014-12-12 | 2019-03-29 | 宜昌人福药业有限责任公司 | A kind of short-acting benzodiazepine salt pharmaceutical composition of injection and preparation method thereof |
| CN106892924B (en) * | 2015-12-17 | 2021-01-08 | 四川科伦博泰生物医药股份有限公司 | Short-acting benzodiazepine derivatives, method for the production thereof and use thereof |
| CN107266452A (en) * | 2016-04-08 | 2017-10-20 | 四川科伦药物研究院有限公司 | The salt and its crystal form, preparation method and purposes of benzodiazepine * derivatives |
| BR112018071082A2 (en) | 2016-04-14 | 2019-02-05 | Paion Uk Ltd | nasal and orally inhaled benzodiazepines |
| CN108264499B (en) * | 2017-01-04 | 2020-10-20 | 江苏恒瑞医药股份有限公司 | Preparation method of benzodiazepine derivative |
| EP3580219B1 (en) | 2017-02-09 | 2022-04-13 | Assia Chemical Industries Ltd. | Process for the preparation of remimazolam and solid state forms of remimazolam salts |
| ES2697918A1 (en) * | 2017-07-28 | 2019-01-29 | Moehs Iberica Sl | PROCEDURE FOR PREPARING METHYL ESTER OF ACID 3 - [(3S) -7-BROMO-2-OXO-5- (PYRIDIN-2-IL) -2,3-DIHYDRO-1H- [1,4] -BENZODIAZEPIN-3- IL] PROPIONIC, AND USEFUL COMPOUNDS IN THAT PROCEDURE (Machine-translation by Google Translate, not legally binding) |
| ES2709298B2 (en) | 2017-10-13 | 2019-08-21 | Moehs Iberica Sl | PROCEDURE TO PREPARE METHYL ESTER ACID 3 - [(4S) -8-BROMO-1-METHYL-6- (PIRIDIN-2-IL) -4H-IMIDAZO [1,2-A] [1,4] BENZODIAZEPIN-4 -IL] -PROPIONIC, AND USEFUL COMPOUNDS IN THAT PROCEDURE |
| CN108033964B (en) * | 2017-12-28 | 2021-02-09 | 杭州奥默医药股份有限公司 | Pyridyl imidazobenzodiazepine propionate compound and synthesis and application thereof |
| ES2827125A1 (en) * | 2019-11-19 | 2021-05-19 | Moehs Iberica Sl | USEFUL INTERMEDIATE IN THE PREPARATION OF REMIMAZOLAM, ITS OBTAINING PROCEDURE, AND ITS USE IN THE OBTAINING OF REMIMAZOLAM (Machine-translation by Google Translate, not legally binding) |
| KR102526590B1 (en) * | 2020-06-19 | 2023-04-28 | 하나제약 주식회사 | METHOD FOR PREPARATION OF 3-[(4S)-8-BROMO-1-METHYL-6-(2-PYRIDINYL)-4H-IMIDAZO[1,2-a][1,4]BENZODIAZEPINE-4-YL]PROPIONIC ACID METHYL ESTER |
| CN112358483A (en) * | 2020-11-09 | 2021-02-12 | 中国药科大学 | Novel benzodiazepine compound, preparation method and application thereof |
| CN112321594B (en) * | 2020-12-07 | 2022-05-20 | 扬子江药业集团有限公司 | Preparation method of benzodiazepine medicine |
| CN114644612B (en) * | 2020-12-17 | 2023-04-28 | 成都苑东生物制药股份有限公司 | Preparation method of benzodiazepine nerve inhibitor intermediate compound |
| CN113717176B (en) * | 2021-10-09 | 2022-07-05 | 上海再启生物技术有限公司 | Method for preparing remazolam |
| CN114014839A (en) * | 2021-12-16 | 2022-02-08 | 上海再启生物技术有限公司 | Method for preparing key intermediate of remimazolam |
| WO2023194945A1 (en) | 2022-04-08 | 2023-10-12 | Fresenius Kabi Oncology Ltd. | An improved process for the preparation of remimazolam |
| CN115385891A (en) * | 2022-09-06 | 2022-11-25 | 上海药坦药物研究开发有限公司 | Preparation method of remazolam intermediate |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6440959B1 (en) | 1999-04-21 | 2002-08-27 | Hoffman-La Roche Inc. | Pyrazolobenzodiazepines |
| GB9911152D0 (en) | 1999-05-14 | 1999-07-14 | Glaxo Group Ltd | Short-acting benzodiazepines |
| CA2583536A1 (en) | 2004-10-13 | 2006-04-27 | Merck & Co., Inc. | Cgrp receptor antagonists |
| DE602006014097D1 (en) * | 2005-01-18 | 2010-06-17 | Merck Sharp & Dohme | CGRP RECEPTOR ANTAGONISTS |
| GB0613692D0 (en) * | 2006-07-10 | 2006-08-16 | Cenes Ltd | Benzodiazepine salts |
| PL2081921T3 (en) | 2006-07-10 | 2011-03-31 | Paion Uk Ltd | Short-acting benzodiazepine salts and their polymorphic forms |
| GB0613693D0 (en) | 2006-07-10 | 2006-08-16 | Cenes Ltd | Benzodiazepine salts (3) |
| PL2155712T3 (en) * | 2007-05-22 | 2017-02-28 | Chemocentryx, Inc. | 3-(imidazolyl)-pyrazolo[3,4-b]pyridines |
| WO2009145323A1 (en) | 2008-05-30 | 2009-12-03 | 日産化学工業株式会社 | Method for oxidizing alcohol by using polycyclic compound |
| WO2010043240A1 (en) | 2008-10-16 | 2010-04-22 | Paion Uk Limited | Administration scheme of polar opioid metabolites for post-operative pain management |
| WO2010116794A1 (en) | 2009-03-30 | 2010-10-14 | 日本製紙株式会社 | Method for recovery/reuse of n-oxyl compound |
| EP2305647A1 (en) | 2009-09-18 | 2011-04-06 | PAION UK Limited | Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process |
| JP5635275B2 (en) | 2010-01-28 | 2014-12-03 | 日清紡ホールディングス株式会社 | Alcohol oxidation method |
| EP2450039A1 (en) | 2010-11-08 | 2012-05-09 | PAION UK Ltd. | Dosing regimen for sedation with CNS 7056 (Remimazolam) |
| ES2651389T3 (en) | 2012-05-22 | 2018-01-26 | Paion Uk Limited | Compositions comprising short-acting benzodiazepines |
| SG11201501358SA (en) | 2012-08-31 | 2015-04-29 | Paion Uk Ltd | Method for administering hypnotic/sedative agent |
| AR094963A1 (en) | 2013-03-04 | 2015-09-09 | Ono Pharmaceutical Co | EXCELLENT OXIDATION REACTION IN THE CONVERSION INDEX |
-
2009
- 2009-09-18 EP EP09011914A patent/EP2305647A1/en not_active Withdrawn
-
2010
- 2010-09-15 US US13/496,742 patent/US9156842B2/en active Active
- 2010-09-15 ES ES10760917.4T patent/ES2555233T3/en active Active
- 2010-09-15 CN CN201080049975.3A patent/CN102753525B/en active Active
- 2010-09-15 JP JP2012529154A patent/JP5801309B2/en active Active
- 2010-09-15 PT PT107609174T patent/PT2477967E/en unknown
- 2010-09-15 KR KR1020127009891A patent/KR101801735B1/en active IP Right Grant
- 2010-09-15 PL PL10760917T patent/PL2477967T3/en unknown
- 2010-09-15 DK DK10760917.4T patent/DK2477967T3/en active
- 2010-09-15 BR BR112012006053-8A patent/BR112012006053B1/en active IP Right Grant
- 2010-09-15 CA CA2774018A patent/CA2774018C/en active Active
- 2010-09-15 AU AU2010294873A patent/AU2010294873B2/en active Active
- 2010-09-15 WO PCT/EP2010/005668 patent/WO2011032692A1/en active Application Filing
- 2010-09-15 RU RU2012115456/04A patent/RU2551848C2/en active
- 2010-09-15 HU HUE10760917A patent/HUE028298T2/en unknown
- 2010-09-15 EP EP10760917.4A patent/EP2477967B1/en active Active
- 2010-09-15 MX MX2015018057A patent/MX341093B/en unknown
- 2010-09-15 MX MX2012003183A patent/MX337683B/en active IP Right Grant
-
2012
- 2012-12-24 HK HK12113326.4A patent/HK1173437A1/en unknown
-
2015
- 2015-09-01 US US14/841,899 patent/US9512078B2/en active Active
- 2015-12-03 HR HRP20151316TT patent/HRP20151316T1/en unknown
-
2016
- 2016-10-27 US US15/336,143 patent/US10000464B2/en active Active
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